- Synthesis process of (2R')-2'-deoxyl-2'-fluoro-2'-methyluridine
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The invention discloses a synthesis process of (2R')-2'-deoxyl-2'-fluoro-2'-methyluridine, relates to the technical field of synthesis of medicines, and solves the technical problems of high cost andlow product yield of the existing process. According to the synthesis process, sodium borohydride or potassium borohydride is used for reducing ribose lactone, so that an expensive reductive reagent which is sodium dihydro-bis-(2-methoxyethoxy)aluminate or lithium tri-tert-butoxyaluminum hydride is not used, and the cost is greatly reduced; N,O-bis(trimethylsilyl)acetamide is used as a silicon etherification reagent, so that the yield of glycosylation reaction is increased; the product yield can reach 85-90% and is far higher than that in route III by 58%; the product yield is obviously increased; hydroxyl at the 5' site is protected, so that side reaction in ring-closing reaction can be avoided; meanwhile, a common polar solvent which is dimethylformamide is used; the product yield undercatalysis of sodium hydrogen carbonate can reach 87-92%. The synthesis process is easy to operate; the process condition is more easily controlled; the cost is reduced; the synthesis process is applicable to large-batch production.
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- Synthesis and Evaluation of 2,6-Modified Purine 2′-C-Methyl Ribonucleosides as Inhibitors of HCV Replication
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A variety of 2,6-modified purine 2′-C-methylribonucleosides and their phosphoramidate prodrugs were synthesized and evaluated for inhibition of HCV RNA replication in Huh-7 cells and for cytotoxicity in various cell lines. Cellular pharmacology and HCV polymerase incorporation studies on the most potent and selective compound are reported.
- Zhou, Longhu,Zhang, Hongwang,Tao, Sijia,Ehteshami, Maryam,Cho, Jong Hyun,McBrayer, Tamara R.,Tharnish, Philip,Whitaker, Tony,Amblard, Franck,Coats, Steven J.,Schinazi, Raymond F.
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- PROCESS FOR THE PREPARATION OF RIBOFURANOSE DERIVATIVES
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The present invention relates to a new process in 3 steps starting from 2-C-methyl-D-ribopentono-1,4-lactone for the preparation of tetra-acyl ribofuranose derivatives of Formula (I) useful in the synthesis of nucleotides.
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Page 16-17; 22
(2008/06/13)
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- Process for the preparation of ribofuranose derivatives
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The present invention relates to a new process in 3 steps starting from 2-C-methyl-D-ribopentono-1,4-lactone for the preparation of tetra-acyl ribofuranose derivatives of formula (I): useful in the synthesis of nucleotides.
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- A short, flexible route toward 2'-C-branched ribonucleosides
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A five-step synthesis of 2'-C-branched ribonucleosides from commercially obtained 1,3,5-tri-O-benzoyl-α-D-ribofuranose (4) is described. The free hydroxyl group of 4 was oxidized in high yield with Dess-Martin periodane reagent. The resultant 2-ketosugar was treated with MeMgBr/TiCl4, CH2=CHMgBr/CeCl3, or TMSC≡CLi/CeCl3, and in each case addition to the ketone proceeded stereoselectively to provide 2-alkylated ribofuranosides. After conversion to the corresponding tetrabenzoyl derivatives, the 2-alkylribofuranosides were coupled to nucleobases under Vorbruggen persilylation conditions, giving the β-nucleosides with high stereoselectivity. Deprotection with methanolic ammonia provided the title compounds in 17-49% overall yields from 4.
- Harry-O'kuru,Smith,Wolfe
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p. 1754 - 1759
(2007/10/03)
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- 2′-C-alkylribonucleosides: Design, synthesis, and conformation
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Certain 2′-C-alkylribonucleotides have been designed as potential mechanism-based inactivators of ribonucleotide reductases. A short, flexible route toward the corresponding nucleosides and NMR evidence concerning their preferred solution conformations are discussed. Copyright
- Harry-O'kuru, Rogers E.,Kryjak, Emily A.,Wolfe, Michael S.
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p. 1457 - 1460
(2007/10/03)
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- A concise synthesis of 2'-C-methylribonucleosides
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2'-C-methylribonucleosides were synthesized in five steps from commercially available 1,3,5-tri-O-benzoyl-α-D-ribose with good overall yields.
- Wolfe,Harry-O'kuru
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p. 7611 - 7614
(2007/10/02)
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